EP0533933A1 - Bisheterocyklische verbindung - Google Patents
Bisheterocyklische verbindung Download PDFInfo
- Publication number
- EP0533933A1 EP0533933A1 EP91912078A EP91912078A EP0533933A1 EP 0533933 A1 EP0533933 A1 EP 0533933A1 EP 91912078 A EP91912078 A EP 91912078A EP 91912078 A EP91912078 A EP 91912078A EP 0533933 A1 EP0533933 A1 EP 0533933A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- methyl
- bis
- dioxo
- phenoxy
- thiazolidinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 0 CC(C)C(*)C(*)(*C(N1)=*)C1=O Chemical compound CC(C)C(*)C(*)(*C(N1)=*)C1=O 0.000 description 11
- URLKBWYHVLBVBO-UHFFFAOYSA-N Cc1ccc(C)cc1 Chemical compound Cc1ccc(C)cc1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- VBAPYXHNMYKBKN-UHFFFAOYSA-N CC(CC1)CCC1OC Chemical compound CC(CC1)CCC1OC VBAPYXHNMYKBKN-UHFFFAOYSA-N 0.000 description 1
- YTRAUCVHOGVEGR-UHFFFAOYSA-N CC1NNNN1 Chemical compound CC1NNNN1 YTRAUCVHOGVEGR-UHFFFAOYSA-N 0.000 description 1
- JFKRSIYDVSWBFV-UHFFFAOYSA-N CC1SC(N)NC1O Chemical compound CC1SC(N)NC1O JFKRSIYDVSWBFV-UHFFFAOYSA-N 0.000 description 1
- CIAYBBUZNBDIDM-UHFFFAOYSA-N CCCCCCOc1ccc(CI)cc1 Chemical compound CCCCCCOc1ccc(CI)cc1 CIAYBBUZNBDIDM-UHFFFAOYSA-N 0.000 description 1
- HXDOZKJGKXYMEW-UHFFFAOYSA-N CCc(cc1)ccc1O Chemical compound CCc(cc1)ccc1O HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N Cc(cc1)ccc1O Chemical compound Cc(cc1)ccc1O IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 1
- OBEZUVUNLPTBLE-UHFFFAOYSA-N Cc(cc1)ccc1OCCCCCOc1ccc(C=[IH])cc1 Chemical compound Cc(cc1)ccc1OCCCCCOc1ccc(C=[IH])cc1 OBEZUVUNLPTBLE-UHFFFAOYSA-N 0.000 description 1
- OBEOBNWODZWIRZ-UHFFFAOYSA-N Cc(cc1)ccc1SCCCCCSc1ccc(C)cc1 Chemical compound Cc(cc1)ccc1SCCCCCSc1ccc(C)cc1 OBEOBNWODZWIRZ-UHFFFAOYSA-N 0.000 description 1
- XAFAKOAAAHXCAY-UHFFFAOYSA-N O=C(CCNC1=O)SC1I Chemical compound O=C(CCNC1=O)SC1I XAFAKOAAAHXCAY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D291/00—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms
- C07D291/02—Heterocyclic compounds containing rings having nitrogen, oxygen and sulfur atoms as the only ring hetero atoms not condensed with other rings
- C07D291/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D263/46—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/36—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/40—Unsubstituted amino or imino radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/54—Nitrogen and either oxygen or sulfur atoms
Definitions
- the compounds (I) of the present invention may have asymmetric carbon atoms and, in such cases, they may occur as isomers. Such optical and other stereoisomers as well as mixtures thereof also fall within the scope of the present invention.
- the starting compound (II) can be obtained, for example as follows.
- the compound (I) and salts thereof of the present invention have exceedingly high hypoglycemic potencies due to their action to potentiate the sensitivity to insulin and are low in toxicity. Therefore, they are of use as prophylactic and therapeutic agents for diabetes, particularly non-insulin-dependent diabetes mellitus (type II), and various diabetic complications, as well as for combination therapy with insulin.
- the insoluble precipitate was recovered by filtration and recrystallized from dimethylformamide to give 2.6 g of 1-[4-[(2,4-dioxo-5-thiazolididene)methyl]phenoxy]-5-[4-(5-rhodanylidene)methyl]phenoxy]pentane, m.p. ⁇ 310°C.
- This precipitate was suspended in 10 ml of dimethylimidazolidinone followed by addition of 2.5 g of sodium borohydride, and the mixture was heated at 60-70°C for 12 hours. The reaction mixture was dispersed in 100 ml of water and extracted with 200 ml of ethyl acetate.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP176550/90 | 1990-07-03 | ||
| JP17655090 | 1990-07-03 | ||
| JP11418491 | 1991-02-22 | ||
| JP114184/91 | 1991-02-22 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP0533933A1 true EP0533933A1 (de) | 1993-03-31 |
| EP0533933A4 EP0533933A4 (en) | 1993-05-05 |
Family
ID=26453004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP19910912078 Withdrawn EP0533933A4 (en) | 1990-07-03 | 1991-07-01 | Bisheterocyclic compound |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP0533933A4 (de) |
| KR (1) | KR930701436A (de) |
| AU (1) | AU650465B2 (de) |
| CA (1) | CA2086606A1 (de) |
| FI (1) | FI925980A0 (de) |
| HU (1) | HUT65619A (de) |
| PL (1) | PL296945A1 (de) |
| WO (1) | WO1992000967A1 (de) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995014673A1 (en) * | 1993-11-22 | 1995-06-01 | Pharmacia S.P.A. | 4,5-diphenylimidazole derivatives, their preparation and their use as acyl coenzyme a: cholesterol-0-acyl-transferase (acat) inhibitor |
| US7041693B2 (en) | 2002-10-04 | 2006-05-09 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme (TACE) |
| EP1917962A1 (de) | 1998-11-12 | 2008-05-07 | Smithkline Beecham Plc | Pharmazeutische Zusammensetzung zur modifizierten Freisetzung eines Insulinsensibilisators. |
| EP1992337A1 (de) | 1998-11-12 | 2008-11-19 | Smithkline Beecham Plc | Neue Zusammensetzung mit modifizierten Freisetzung der Wirkstoffe |
| EP2036554A1 (de) | 2000-06-19 | 2009-03-18 | SmithKline Beecham plc | Zusammensetzungen zur Behandlung von Diabetes welche Dipeptidylpeptidase Inhibitoren und ein anderes Antidiabetikum enthalten |
| EP2266576A1 (de) | 1997-06-18 | 2010-12-29 | SmithKline Beecham Limited | Behandlung der diabetes mit thiazolidindione und sulphonylurea |
| US7976871B2 (en) | 2002-08-05 | 2011-07-12 | Torrent Pharmaceuticals Limited | Modified release composition of highly soluble drugs |
| US8268352B2 (en) | 2002-08-05 | 2012-09-18 | Torrent Pharmaceuticals Limited | Modified release composition for highly soluble drugs |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69228122T2 (de) * | 1991-07-30 | 1999-06-24 | Yamanouchi Pharma Co Ltd | Neues bisheterocyclisches derivat und salz und hypoglykämische zusammensetzung |
| DE4317320A1 (de) * | 1993-05-25 | 1994-12-01 | Boehringer Mannheim Gmbh | Neue Thiazolidindione und diese enthaltende Arzneimittel |
| ES2154551B1 (es) * | 1998-08-03 | 2001-10-16 | Vita Invest Sa | Nuevos derivados de tetrazol como agentes antidiabeticos. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0397453A1 (de) * | 1989-05-09 | 1990-11-14 | Beecham Group p.l.c. | Bis-2,4-Dioxothiazolidine |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5661366A (en) * | 1979-10-23 | 1981-05-26 | Doujin Kagaku Kenkyusho:Kk | Bistetrazolium salt compound |
| US4338452A (en) * | 1980-09-17 | 1982-07-06 | Eli Lilly And Company | 1-and 2-(1-Alkyl-1H-tetrazol-5-yl-methyl)-1H-tetrazol-5-thiols and 1-cyanomethyl tetrazole-5-thiol |
| US4659801A (en) * | 1985-12-10 | 1987-04-21 | Minnesota Mining And Manufacturing Company | Thiazolinethione-containing polymer |
-
1991
- 1991-07-01 HU HU9204176A patent/HUT65619A/hu unknown
- 1991-07-01 KR KR1019920703427A patent/KR930701436A/ko not_active Application Discontinuation
- 1991-07-01 PL PL29694591A patent/PL296945A1/xx unknown
- 1991-07-01 CA CA002086606A patent/CA2086606A1/en not_active Abandoned
- 1991-07-01 EP EP19910912078 patent/EP0533933A4/en not_active Withdrawn
- 1991-07-01 AU AU80795/91A patent/AU650465B2/en not_active Ceased
- 1991-07-01 WO PCT/JP1991/000887 patent/WO1992000967A1/ja not_active Application Discontinuation
-
1992
- 1992-12-31 FI FI925980A patent/FI925980A0/fi not_active Application Discontinuation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0397453A1 (de) * | 1989-05-09 | 1990-11-14 | Beecham Group p.l.c. | Bis-2,4-Dioxothiazolidine |
Non-Patent Citations (1)
| Title |
|---|
| See also references of WO9200967A1 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995014673A1 (en) * | 1993-11-22 | 1995-06-01 | Pharmacia S.P.A. | 4,5-diphenylimidazole derivatives, their preparation and their use as acyl coenzyme a: cholesterol-0-acyl-transferase (acat) inhibitor |
| EP2266576A1 (de) | 1997-06-18 | 2010-12-29 | SmithKline Beecham Limited | Behandlung der diabetes mit thiazolidindione und sulphonylurea |
| EP1917962A1 (de) | 1998-11-12 | 2008-05-07 | Smithkline Beecham Plc | Pharmazeutische Zusammensetzung zur modifizierten Freisetzung eines Insulinsensibilisators. |
| EP1992337A1 (de) | 1998-11-12 | 2008-11-19 | Smithkline Beecham Plc | Neue Zusammensetzung mit modifizierten Freisetzung der Wirkstoffe |
| EP2036554A1 (de) | 2000-06-19 | 2009-03-18 | SmithKline Beecham plc | Zusammensetzungen zur Behandlung von Diabetes welche Dipeptidylpeptidase Inhibitoren und ein anderes Antidiabetikum enthalten |
| US7976871B2 (en) | 2002-08-05 | 2011-07-12 | Torrent Pharmaceuticals Limited | Modified release composition of highly soluble drugs |
| US8216609B2 (en) | 2002-08-05 | 2012-07-10 | Torrent Pharmaceuticals Limited | Modified release composition of highly soluble drugs |
| US8268352B2 (en) | 2002-08-05 | 2012-09-18 | Torrent Pharmaceuticals Limited | Modified release composition for highly soluble drugs |
| US7041693B2 (en) | 2002-10-04 | 2006-05-09 | Bristol-Myers Squibb Company | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme (TACE) |
Also Published As
| Publication number | Publication date |
|---|---|
| FI925980A (fi) | 1992-12-31 |
| WO1992000967A1 (fr) | 1992-01-23 |
| PL296945A1 (de) | 1992-07-13 |
| CA2086606A1 (en) | 1992-01-04 |
| KR930701436A (ko) | 1993-06-11 |
| EP0533933A4 (en) | 1993-05-05 |
| HU9204176D0 (en) | 1993-04-28 |
| HUT65619A (en) | 1994-07-28 |
| AU650465B2 (en) | 1994-06-23 |
| AU8079591A (en) | 1992-02-04 |
| FI925980A0 (fi) | 1992-12-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4687777A (en) | Thiazolidinedione derivatives, useful as antidiabetic agents | |
| KR930008450B1 (ko) | 벤즈옥사졸유도체 및 이의 제조방법 | |
| KR950011120B1 (ko) | 리폭시게나제 억제 화합물 및 이를 함유하는 약제학적 조성물 | |
| SU1400508A3 (ru) | Способ получени производных арилтиазолов | |
| EA009518B1 (ru) | Соединения, модулирующие активность ppar, и способы их получения | |
| JP3036853B2 (ja) | 炎症性腸疾患治療に有用な化合物 | |
| CZ397598A3 (cs) | Derivát 5-fenoxyalkyl-2,4-thiazolidindionu, způsob jeho přípravy, meziprodukty pro jeho přípravu a farmaceutický prostředek, který ho obsahuje | |
| EP0533933A1 (de) | Bisheterocyklische verbindung | |
| WO1999062892A1 (en) | Aminoazole compounds | |
| US5387690A (en) | Method of treating inflammatory bowel disease | |
| KR100198183B1 (ko) | 퀴논기를 함유하는 티아졸리딘 화합물, 이의 제조방법 및 치료용도 | |
| EP0597102B1 (de) | Neues bisheterocyclisches derivat und salz und hypoglykämische zusammensetzung | |
| WO2001005776A1 (fr) | Derives d'aminothiazole et leur utilisation comme ligands des recepteurs crf | |
| GB2038822A (en) | Thiazole derivatives | |
| EP0348257A2 (de) | (Hetero)Aryl-diazol-Derivate, Verfahren zu deren Herstellung und deren Verwendung in der Therapie | |
| US4735961A (en) | Oxazoles and thiazoles containing an aminohydroxypropoxyphenyl moiety | |
| US4845231A (en) | Tetrazoles and their use as hypoglycemic agents | |
| PL171273B1 (pl) | Sposób wytwarzania nowych pochodnych tiadiazynonów PL | |
| US4136188A (en) | Treatment of diabetes with 2-substituted-1,3-diazacyclic compounds | |
| US4574127A (en) | Oxazoles and thiazoles containing an aminohydroxypropoxyphenyl moiety | |
| JPS6363670A (ja) | ド−パミン−β−ヒドロキシラ−ゼ抑制剤 | |
| US4707488A (en) | Dopamine-β-hydroxylase inhibitors and use thereof | |
| EP0180500A1 (de) | Thieno- und Furo[2,3-c]pyrrolderivate, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel | |
| US4182865A (en) | Diaza-cyclic derivatives of guanidine | |
| EP0030835B1 (de) | 2-Substituierte-6-phenyl-3(2H)-pyridazinon-Derivate, ihre Herstellung und sie enthaltende pharmazeutische Zusammensetzungen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 19930105 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE |
|
| A4 | Supplementary search report drawn up and despatched |
Effective date: 19930315 |
|
| AK | Designated contracting states |
Kind code of ref document: A4 Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 19960201 |